wahrscheinlich eher "einen an Gefängniskleidung erinnernden Overall". War der Overall vielleicht orange?

The look actually CAME from prison where the incarcerated are not issued belts to keep the pants up that are not custom fitted.
Prison issued clothing tends to be rather baggy, especially the pants that tend to fall off.

= baggy, baglike; hanging loosely. Color is unimportant here.

Ich tendiere zu cassandras Version. Es handelt sich schlicht um "Anstaltskleidung".
Ob diese Kleidung ausgeleiert ist, ergibt sich m.E. nicht aus der Verwendung des Begriffs "prison-issued"

(edit:Die Bedeutung "ausgeleiert" will wohl nur ein Artikel in Men's Health suggerieren...)

Ich denke auch eher, dass es tatsächlich Anstaltskleidung ist und nicht nur so aussieht - zumindest würde ich sonst einen Hinweis im Englischen erwarten. Vielleicht gibt's diese Nato-Shops ja auch für Gefängniszubehör ;-)

Edit: Hier noch Fachtext-Auszug als Beleg dafür, dass es sich um "Anstaltskleidung" handelt -unabhängig von der Passform-:

...the state Trial court unconstitutionally forced him to appear before the jury in prison-issued clothing...;
http://www.ca11.uscourts.gov/unpub/ops/200614...

Definitely actual prison clothing. Have you (wmw) any reason to think otherwise?

• Rather than wear a suit, he appeared every day in a prison-issued green jacket, gray shirt and green pants -- perhaps to draw sympathy from jurors
• The sheriff says he was last seen wearing green work pants, a white T-shirt, brown plaid flannel shirt and prison-issued slippers
• also apologized to the judge for his prison-issued clothing, arriving in the courtroom with his hands chained behind his back and clad in tan jail pants and a white T-shirt
• The women have traded their prison-issued smocks for black jeans and purple work shirts
• an M-16 assault rifle slung across his shoulder, S. checks that other residents have their army-issued weapons ready in case of emergency
• By 8 o'clock, we were snug in our doubled-walled tents, cocooned in heavy, army-issue sleeping bags.
• What looked like a thin, military-issue blanket was draped across his shoulders
• wore a long, bushy gray beard and big black military-issue glasses
• Eating field rations and getting his shut-eye in a military-issue sleeping bag, Denmark's Crown Prince Frederik experienced for himself how his country's troops are faring in Afghanistan
• advised people to wear their own robes rather than drab hospital-issued gowns while fighting illness
• Still wearing his hospital-issued gown, a psychiatric patient didn't travel very far
• be aware of any unfamiliar visitors who are not wearing school-issued security badges
• Her daughter, a sophomore, was given a school-issued calculator without a square-root function for the math test
• with cuffs around their ankles and wrists and standard-issue orange jail shirts draped over their dress clothes
• she realised she was wearing standard-issue aircraft pyjamas and no make-up
• declining to say how the firefighting system was activated and whether personnel aboard had been provided with standard-issue breathing masks
• After completing the paperwork and having his fingerprints and photo taken, C. moved to a private area and changed into a standard-issue blue jail uniform
• Instead of the standard-issue all-black uniform, G., a veteran officer in the city's Uptown 2nd District, chose the powder-blue uniform shirt that he wore to work for more than three decades
• aims to provide U.S. soldiers sent to the frontlines of Iraq and other hotspots with better equipment than substandard government-issue basic personal combat gear
• Pictures have surfaced on the Internet of government-issue tents in prosperous neighborhoods of the little-damaged city of Chengdu
• He wore a team-issued T-shirt, low-cut black socks, all-terrain shoes and baggy shorts
• Racers would use team-issued bikes and give them back at the end of the season
• The Olympic team-issued apparel is strictly controlled by sponsors for this event
http://corpora.informatik.uni-leipzig.de/cgi-...
http://corpora.informatik.uni-leipzig.de/cgi-...

When prisoners enter the prison, they have to give up their street clothes and wear clothing issued (= given out) by the prison. The same goes for soldiers entering the military, or sometimes, students, team members, etc.

Is it the word 'issued' that's confusing? It just means given out or lent by an institution for people to use, but not to keep permanently. You may see either the form X-issued, meaning 'issued by X' (a verb), or X-issue, meaning 'of X issue' (a noun).

Although there are quite a few versions of how sagging was introduced to the fashion arena, sagging pants origin can be traced to the American prison inmates who wore loose fitting prison uniforms without a belt.

http://www.nationalconcernedofficers.com/pant...

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da ist immer noch sagging = schlabberig und prison-issued = Anstaltskleidung, dein Wortpaar passt nicht